Pyridine → HCID 86735210, compound

HRID 1439409Notes

Reaction equation

HRID 1439409 reaction equation
[C:1]([OH:15])(=[O:14])/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].N1C=C[CH:19]=[CH:18][CH:17]=1.S(Cl)(Cl)=O>C1C=CC=CC=1>[CH2:19]([O:14][C:1](=[O:15])/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86735211HCID 86735211, compound

Product 1

HCID 86735210HCID 86735210, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10.2 g of 3,7,11-trimethyl-2-cis/trans, 4-cis/trans, 10-cis/trans-tridecatrienoic acid are dissolved in 65 ml of absolute benzene and 3.5 ml of pyridine and then treated at a temperature between 5° C and 10° C with 3.4 ml of thionyl chloride (dropping time ca 15 minutes). The mixture is subsequently stirred for 1 hour at room temperature, then the liquid is decanted off and the residue is washed out with benzene. The solution is evaporated to dryness under anhydrous conditions. The residue is dissolved in 20 ml of absolute benzene and added dropwise at a temperature between 5° C and 10° C to a solution of 3.6 ml of allyl alcohol and 3.5 ml of pyridine in 50 ml of benzene (dropping time ca 30 minutes). After stirring overnight at room temperature, the solution is diluted with ether and washed with 1-N aqueous hydrochloric acid, then with saturated aqueous sodium bicarbonate solution and finally with sodium chloride solution. After drying, the ether phase is evaporated. The crude product is chromatographed on the 30-fold amount of Kieselgel (eluant: hexane/ether 19:1 parts by volume). 3,7,11-Trimethyl-2-cis/trans, 4-cis/trans, 10-cis/trans-tridecatrienoic acid allyl ester is obtained as a colorless oil of boiling point 120° C/0.05 mmHg (bulb-tube); nD25 = 1.5026.

Workup

  1. customthe liquid is decanted off
  2. washthe residue is washed out with benzene
  3. customThe solution is evaporated to dryness under anhydrous conditions
  4. dissolutionThe residue is dissolved in 20 ml of absolute benzene
  5. additionadded dropwise at a temperature between 5° C and 10° C to a solution of 3.6 ml of allyl alcohol and 3.5 ml of pyridine in 50 ml of benzene (dropping time ca 30 minutes)
  6. stirringAfter stirring overnight at room temperature
  7. additionthe solution is diluted with ether
  8. washwashed with 1-N aqueous hydrochloric acid
  9. customAfter drying
  10. customthe ether phase is evaporated
  11. customThe crude product is chromatographed on the 30-fold amount of Kieselgel (eluant: hexane/ether 19:1 parts by volume)

Sources & evidence

ORD record
ord-b57f307ddec14300aaaf27d13af61439
Source dataset
uspto-grants-1977_11
Patent number
US04059600

Reaction notes

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